How to wear a pencil skirt: 5 Style Panel tips for bringing this staple out of the office

How to Wear a Pencil Skirt Style Panel
How to Wear a Pencil Skirt Style Panel

Nothing satisfies our shopping addiction more than investing in versatile pieces. A tailored pencil skirt easily makes the list of guilt-free purchases. With a variety of colours and styles to choose from, there’s really no excuse for not experimenting with this flattering sartorial staple.

The value of a pencil skirt is perhaps best realized in its ability to take you from day to night. Whether you prefer a classic black midi skirt such as the Calvin Klein style Rooney Mara recently pulled off, or a fun embellished one such as the Burberry Prorsum knee-length skirt Blake Lively dazzled in, the sleek form fitting design combines an office-appropriate length with a nightlife-appropriate wow-factor. Our September cover girl Olivia Wilde knows how to wear a pencil skirt. She recently stunned in this red-checkered A.L.C. midi skirt, giving us all a lesson in print. Wilde paired her skirt with a black leather top and metallic clutch confirming that the styling possibilities for this must-have piece are endless.

For more tips on how to wear a pencil skirt, we’ve turned to our trusted Style Panel. Canadian Fashionista’s Amber Desilets agrees with us that the pencil skirt doesn’t have to be saved for the office. She recommends pairing yours with a simple T-shirt and heels to take this sophisticated style from work-wear to everyday wear. Falling in Style’s Iva Grbesic knows how to wear a pencil skirt. She owns a large assortment of them in colours ranging from navy to neon pink. She recommends thick weights and classic cuts to smooth out the silhouette. All of our Style Panelists agree on one thing. If you don’t own a pencil skirt, you should!

Question 65: How do you style pencil skirts from office wear to everyday wear? Read the answers now! »


How to Wear a Pencil Skirt Barbara Ann Solomon
Photography by Trevor Negin

Barbara Ann Solomon, 26
Toronto | Barbara Ann’s Style Blog

There is nothing that is more perfect for the office environment than a great pencil skirt and blouse. It screams professional and choosing bold prints and colours, it allows you to keep it office appropriate with adding that fashionable flare.

While we are still in the summer months, try to keep the outfit more fun by tying the front rather than tucking it in, it’s more casual and comfortable with the heat.

Barbara Ann’s wearing: Blouse, Joe Fresh. Skirt, Topshop. Wedges, Nine West. Sunglasses, Ray-Bans.

How to Wear a Pencil Skirt Iva Grbesic

Iva Grbesic, 37
Toronto | Falling in Style

I love pencil skirts, I have a large assortment in my closet. From basic navy and black to yellow lace, neon pink, polka dots, textured and stripes. For me they are feminine, practical and easy to wear. I usually wear them dressed up because my daily life is pretty casual. I don’t have an office job and am at home with four children so I have fun with pencil skirts – blouses, peplum, jewelry, chambray, tees. Anything goes for me. Because of my height (I’m six feet tall) they usually hit around my knee. I would love them to be longer but that is a rare find. My favourite pencil skirts are from J Crew because of their fabrication – thick weights and a classic cut that smooths out the silhouette. For this style challenge I opted to take the pencil skirt out for dinner or drinks with your significant other or a great group of girlfriends. I layered jewelled necklaces and chose a pencil skirt in a vibrant striped pattern. This skirt can easily be dressed down with a simple white tee or tank and a pair of sandals/flip flops in a fun metallic. Anyway you style it you’re ready for summer.

How to Wear a Pencil Skirt Amber Desilets

Amber Desilets, 30
London | Canadian Fashionista

The pencil skirt is an elegant, figure-friendly staple in every woman’s wardrobe that doesn’t have to be saved for just the office. By paring it with a simple statement tee and a sexy pair of heels, which will help to elongate the legs and create a slimmer silhouette, you now have the perfect everyday outfit that can take you from day to night.

Amber’s wearing: T-Shirt, Smart Set. Purse, Rebecca Minkoff. Bangle, Cocoa Jewelry. Bracelets, Aldo. Skirt, H&M. Shoes, UrbanOG.

How to Wear a Pencil Skirt Kayla Short

Kayla Short, 26
Halifax | Short Presents

My workplace doesn’t require me to be very dressy, (in fact I tend to overdo it on a regular basis) and so I usually need to tone my favorite pencil skirt down a shade in order to rein in its seriousness and make it work appropriate (for me). I like pairing mine with a causal t-shirt (like this tissue tee from Joe Fresh) and then adding a great little knotted belt.

I probably wouldn’t normally opt for keds, but when heading to the financial district I needed the most responsible looking outfit in my suitcase, but I also needed comfortable shoes. This photo here was snapped while I was touring around NYC, and so my footwear was chosen based on comfort and comfort alone. We literally walked from one end of the city to other sans blisters I might add.

I usually go for an above the knee length skirt because again my office isn’t too serious, but if you’re a meetings kind of gal and you aren’t too petite I’d say go for it. Buying tips for pencil skirts would for sure include fitting your widest part of your body first, and then tailoring the rest. I’m slightly wider in the hips than I am in the waist (no perfect symmetry here), and so I find that pencil skirts tend to ride up on me or bunch up around my hips if they aren’t fitted properly and tapered in at the waist. As long as you fit the biggest part first, you can change the rest to suit your body. Trust me it’s worth the 15-dollar tuck from your tailor.

Kayla’s wearing: Skirt, Tommy Hilfiger. Tissue Tee, Joe Fresh. Shoes, Keds. Sunnies, Ray-Bans.

How to Wear a Pencil Skirt Becky Kung

Becky Kung, 30
Calgary | Velvet & Vino

I love the midi skirt! My favorite thing about this type of skirt is because its street-smart and simply elegant. Given the slightly shorter length, the midi smoothly transitions from office to everyday wear. By its tasteful touch when paired with a blouse, to the snappy look created when paired with a tank top and sandals for the everyday wear.

The most important thing to ask yourself when buying the midi style is are you comfortable by the length and does the length elongate your legs or does it shorten them? This look is not suited for everyone and more importantly, each skirt has it’s own fit and structure, heavily weighing in as to whether it works for your particular body type.

Becky’s wearing: Skirt, Joe Fresh. Blouse, Zara. Heels, Aldo Rise. Handbag, H&M. Belt, H&M.

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